EP1129684B1 - Nanoémulsion à base de lipides amphiphiles et de polymères cationiques et utilisation en cosmétologie - Google Patents
Nanoémulsion à base de lipides amphiphiles et de polymères cationiques et utilisation en cosmétologie Download PDFInfo
- Publication number
- EP1129684B1 EP1129684B1 EP00403527A EP00403527A EP1129684B1 EP 1129684 B1 EP1129684 B1 EP 1129684B1 EP 00403527 A EP00403527 A EP 00403527A EP 00403527 A EP00403527 A EP 00403527A EP 1129684 B1 EP1129684 B1 EP 1129684B1
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- EP
- European Patent Office
- Prior art keywords
- chosen
- nanoemulsion
- alkyl
- nanoemulsion according
- radical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000007908 nanoemulsion Substances 0.000 title claims abstract description 90
- 150000002632 lipids Chemical class 0.000 title claims abstract description 52
- 229920006317 cationic polymer Polymers 0.000 title claims abstract description 19
- 239000002537 cosmetic Substances 0.000 title claims description 12
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 7
- -1 fatty alcohol ethers Chemical class 0.000 claims description 132
- 239000000203 mixture Substances 0.000 claims description 81
- 150000002148 esters Chemical class 0.000 claims description 56
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 229920001296 polysiloxane Polymers 0.000 claims description 35
- 239000003921 oil Substances 0.000 claims description 32
- 239000004094 surface-active agent Substances 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 27
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 26
- 239000000194 fatty acid Substances 0.000 claims description 26
- 229930195729 fatty acid Natural products 0.000 claims description 26
- 239000012071 phase Substances 0.000 claims description 26
- 229930195733 hydrocarbon Natural products 0.000 claims description 25
- 239000004215 Carbon black (E152) Substances 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 20
- 150000001450 anions Chemical group 0.000 claims description 19
- 150000004665 fatty acids Chemical class 0.000 claims description 18
- 210000004209 hair Anatomy 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 12
- 229910019142 PO4 Inorganic materials 0.000 claims description 12
- 150000002194 fatty esters Chemical class 0.000 claims description 12
- 235000021317 phosphate Nutrition 0.000 claims description 12
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 11
- 125000000129 anionic group Chemical group 0.000 claims description 11
- 239000008103 glucose Substances 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- 125000002091 cationic group Chemical group 0.000 claims description 10
- 150000002191 fatty alcohols Chemical class 0.000 claims description 10
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 9
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 229920002678 cellulose Polymers 0.000 claims description 8
- 210000004709 eyebrow Anatomy 0.000 claims description 8
- 210000000720 eyelash Anatomy 0.000 claims description 8
- 210000004400 mucous membrane Anatomy 0.000 claims description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 7
- 229920001400 block copolymer Polymers 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- 235000000346 sugar Nutrition 0.000 claims description 7
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229920000058 polyacrylate Polymers 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 210000004761 scalp Anatomy 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 5
- 150000003863 ammonium salts Chemical group 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 5
- 150000003077 polyols Chemical class 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 239000010775 animal oil Substances 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000002195 fatty ethers Chemical class 0.000 claims description 4
- 239000003760 tallow Substances 0.000 claims description 4
- 230000008719 thickening Effects 0.000 claims description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- YSJGOMATDFSEED-UHFFFAOYSA-M behentrimonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCCCCC[N+](C)(C)C YSJGOMATDFSEED-UHFFFAOYSA-M 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000003093 cationic surfactant Substances 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- CYFHLEMYBPQRGN-UHFFFAOYSA-N ditetradecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCC CYFHLEMYBPQRGN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000002480 mineral oil Substances 0.000 claims description 3
- 150000002823 nitrates Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229920000223 polyglycerol Polymers 0.000 claims description 3
- 229940057429 sorbitan isostearate Drugs 0.000 claims description 3
- 229950004959 sorbitan oleate Drugs 0.000 claims description 3
- 230000000699 topical effect Effects 0.000 claims description 3
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- ATFFFUXLAJBBDE-FQEVSTJZSA-N N-Stearoyl glutamic acid Chemical compound CCCCCCCCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCC(O)=O ATFFFUXLAJBBDE-FQEVSTJZSA-N 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- AVTXVDFKYBVTKR-DPAQBDIFSA-N [(3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] dihydrogen phosphate Chemical class C1C=C2C[C@@H](OP(O)(O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 AVTXVDFKYBVTKR-DPAQBDIFSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 claims description 2
- BHYOQNUELFTYRT-DPAQBDIFSA-N cholesterol sulfate Chemical class C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 BHYOQNUELFTYRT-DPAQBDIFSA-N 0.000 claims description 2
- RNPXCFINMKSQPQ-UHFFFAOYSA-N dicetyl hydrogen phosphate Chemical class CCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCC RNPXCFINMKSQPQ-UHFFFAOYSA-N 0.000 claims description 2
- DKJLEUVQMKPSHB-UHFFFAOYSA-N dimethyl-[3-(octadecanoylamino)propyl]-(2-oxo-2-tetradecoxyethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCCCC DKJLEUVQMKPSHB-UHFFFAOYSA-N 0.000 claims description 2
- UCYFZDNMZYZSPN-UHFFFAOYSA-N docosyl(trimethyl)azanium Chemical class CCCCCCCCCCCCCCCCCCCCCC[N+](C)(C)C UCYFZDNMZYZSPN-UHFFFAOYSA-N 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229920002401 polyacrylamide Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 150000003903 lactic acid esters Chemical class 0.000 claims 2
- 150000008163 sugars Chemical class 0.000 claims 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- IOUUIFSIQMVYKP-UHFFFAOYSA-N Tetradecyl acetate Chemical class CCCCCCCCCCCCCCOC(C)=O IOUUIFSIQMVYKP-UHFFFAOYSA-N 0.000 claims 1
- 150000001449 anionic compounds Chemical class 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 229940093541 dicetylphosphate Drugs 0.000 claims 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 claims 1
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 claims 1
- 230000001815 facial effect Effects 0.000 claims 1
- 229910001412 inorganic anion Inorganic materials 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 claims 1
- 150000002891 organic anions Chemical class 0.000 claims 1
- 239000010773 plant oil Substances 0.000 claims 1
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 description 58
- 239000000047 product Substances 0.000 description 23
- 235000019198 oils Nutrition 0.000 description 22
- 239000000839 emulsion Substances 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 19
- 125000004429 atom Chemical group 0.000 description 18
- 235000011187 glycerol Nutrition 0.000 description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 235000001727 glucose Nutrition 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 9
- 150000002170 ethers Chemical class 0.000 description 8
- RMTFNDVZYPHUEF-XZBKPIIZSA-N 3-O-methyl-D-glucose Chemical compound O=C[C@H](O)[C@@H](OC)[C@H](O)[C@H](O)CO RMTFNDVZYPHUEF-XZBKPIIZSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 229920013822 aminosilicone Polymers 0.000 description 7
- 210000003491 skin Anatomy 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical class [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 description 6
- 235000010980 cellulose Nutrition 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000004530 micro-emulsion Substances 0.000 description 6
- 239000002304 perfume Substances 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 235000015165 citric acid Nutrition 0.000 description 5
- 239000006210 lotion Substances 0.000 description 5
- 210000000282 nail Anatomy 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- 150000002942 palmitic acid derivatives Chemical class 0.000 description 5
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 4
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- 150000003893 lactate salts Chemical class 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 229930091371 Fructose Natural products 0.000 description 3
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 3
- 239000005715 Fructose Substances 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- 241000209504 Poaceae Species 0.000 description 3
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 3
- 244000044822 Simmondsia californica Species 0.000 description 3
- 235000004433 Simmondsia californica Nutrition 0.000 description 3
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
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- 239000001272 nitrous oxide Substances 0.000 description 1
- 229940073555 nonoxynol-10 Drugs 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
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- 235000019645 odor Nutrition 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940101267 panthenol Drugs 0.000 description 1
- 235000020957 pantothenol Nutrition 0.000 description 1
- 239000011619 pantothenol Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229950011087 perflunafene Drugs 0.000 description 1
- UWEYRJFJVCLAGH-UHFFFAOYSA-N perfluorodecalin Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C21F UWEYRJFJVCLAGH-UHFFFAOYSA-N 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
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- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 235000020944 retinol Nutrition 0.000 description 1
- 239000011607 retinol Substances 0.000 description 1
- 229960003471 retinol Drugs 0.000 description 1
- 235000019172 retinyl palmitate Nutrition 0.000 description 1
- 239000011769 retinyl palmitate Substances 0.000 description 1
- 229940108325 retinyl palmitate Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
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- 229940098760 steareth-2 Drugs 0.000 description 1
- 229940100459 steareth-20 Drugs 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229940077400 trideceth-12 Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
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Classifications
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
- A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/731—Cellulose; Quaternized cellulose derivatives
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
- A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
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- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/21—Emulsions characterized by droplet sizes below 1 micron
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- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
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- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
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- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
Definitions
- the present invention relates to an oil-in-water nanoemulsion whose oil globules have a mean size of less than 150 nm and comprising at least one amphiphilic lipid preferably nonionic or anionic and at least one cationic polymer comprising at least one hydrophobic sequence and at least one hydrophilic sequence and their use in topical application especially in cosmetics and dermopharmacy.
- Oil-in-water emulsions are well known in the field of cosmetics and dermopharmacy, in particular for the preparation of cosmetic products such as lotions, tonics, serums, toilet waters.
- compositions are generally unstable in storage and the cosmetic properties are insufficient.
- application of such compositions on the hair leads to a greasy feel, a difficulty of rinsing.
- dried hair is without volume and has a loaded feel.
- nanoemulsion it is meant a metastable O / W emulsion, the size of the oily globules of which is less than 150 nm, oily globules stabilized by a ring of amphiphilic lipids that may optionally form a liquid crystal phase of lamellar type located at the oil / phase interface aqueous.
- the transparency of these emulsions comes from the small size of the oily globules, a small size obtained thanks to the use in particular of a high-pressure homogenizer.
- Nanoemulsions are to be distinguished from microemulsions by their structure.
- Microemulsions are thermodynamically stable dispersions consisting of micelles of lipid (s) amphiphilic (s) swollen by oil. In addition microemulsions do not require significant mechanical energy to be performed. They form spontaneously by simply contacting the constituents.
- the major disadvantages of microemulsions are related to their high proportion of surfactants, leading to intolerances and resulting in a sticky feel when applied to the skin. Moreover, their range of formulation is generally very narrow and their temperature stability very limited.
- amphiphilic lipid phase is composed of one or more (mixture) nonionic and / or ionic amphiphilic lipid.
- Amphiphilic lipid means any molecule having a bipolar structure comprising at least one hydrophobic part and at least one hydrophilic part having the property of reducing the surface tension of water ( ⁇ ⁇ 55mN / m) and reducing the interfacial tension between water and an oily phase.
- the synonyms of amphiphilic lipid are, for example: surfactant, surfactant, emulsifier.
- Nanoemulsions comprising an amphiphilic lipid phase consisting of phospholipids, a cationic lipid, water and a hydrophobic sunscreen are known in the state of the art. They are obtained by a high pressure homogenization process. These emulsions have the disadvantage of being unstable at storage at traditional storage temperatures, namely between 0 and 45 ° C. They lead to yellow compositions and produce rancid odors that develop after a few days of storage. In addition, these emulsions do not provide good cosmetic properties. They are described in the magazine "DCI" of April 1996, pages 46-48.
- EP-A-728 460 and EP-A-780 114 describe nanoemulsions based on fluid non-ionic amphiphilic lipids or silicone surfactants.
- nanoemulsions are fluid.
- these products must have a certain consistency or viscosity. Indeed, a liquid product is much more difficult to dose and flows easily between the fingers.
- aqueous media water-soluble or water-dispersible polymers, and in particular optionally crosslinked polymers such as polycarboxyvinyl acids and especially carbopols, said polymers preferably having a long chain length and a high molecular weight.
- a thickening system for thickening or even gelling suitably a composition in the form of oil-in-water nanoemulsion, without affecting the cosmetic properties of said compositions.
- the Applicant has unexpectedly discovered that it is possible to thicken the nanoemulsions comprising an oily phase dispersed in an aqueous phase whose oil globules have a mean size of less than 150 nm, with cationic polymers that are preferably water-soluble or water-dispersible. comprising at least one hydrophobic block and at least one hydrophilic block.
- the subject of the present invention is oil-in-water nanoemulsions comprising an oily phase dispersed in an aqueous phase, the oil globules of which have an average size in number of less than 150 nm, characterized in that they comprise at least one oil, at least one amphiphilic lipid, preferably nonionic or anionic and at least one cationic polymer, preferably water-soluble or water-dispersible, comprising at least one hydrophobic block and at least one hydrophilic block and that the weight ratio of the quantity of oil the amount of amphiphilic lipid is between 1 and 10 and preferably between 1.2 and 6.
- Another subject of the invention is a process for thickening oil-in-water nanoemulsions having oil globules whose number average size is less than 150 nm, in which a cationic polymer is added to said composition, preferably water-soluble or water-dispersible, comprising at least one hydrophobic block and at least one hydrophilic block.
- the increase in the viscosity of the medium results from the formation of a network of oil particles, said network involving associations of the type hydrophobic between, on the one hand, the hydrophobic groups of the polymer and, on the other hand, the hydrophobic cores of the oil particles.
- the existence of labile bonds between the particles causes an increase in the viscosity of the mixture.
- the nanoemulsions according to the invention are prepared at temperatures between 4 and 45 ° C. and are compatible with heat-sensitive active agents. They may contain significant amounts of oil. They can in particular contain significant amounts of perfume and improve their persistence. They also promote the penetration of active ingredients into the superficial layers of the skin and the deposition of active ingredients on keratinous fibers such as the hair. The hair treated with these nanoemulsions is shiny without a touch or a greasy appearance, they disentangle easily, are softer and more nervous.
- the cationic polymers preferably water-soluble or water-dispersible, comprise at least one hydrophobic block and at least one hydrophilic block.
- the cationic polymer comprises at least two hydrophobic sequences.
- the hydrophobic block (s) are (are) mainly fatty chains having from 6 to 30 carbon atoms, in particular hydrocarbon-based compounds such as alkyl, arylalkyl, alkylaryl, alkenyl, divalent aliphatic groups such as C4-C30 alkylene, divalent cycloaliphatic groups such as in particular methylenedicyclohexyl, isophorone or divalent aromatic groups such as phenylene.
- hydrocarbon-based compounds such as alkyl, arylalkyl, alkylaryl, alkenyl, divalent aliphatic groups such as C4-C30 alkylene, divalent cycloaliphatic groups such as in particular methylenedicyclohexyl, isophorone or divalent aromatic groups such as phenylene.
- the hydrophilic block or sequences may be, inter alia, polyethylene oxide, polysaccharide, polyamide, especially polyacrylamide, polyester and mixtures thereof and preferably polyethylene oxide having from 15 to 500 ethylene oxides.
- the cationic polymer comprises at least one tertiary or quaternary amine group.
- the link (s) between the hydrophobic and hydrophilic sequence is most often, without being limiting, of the ester, ether, urea, amide or urethane type and mixtures thereof.
- the ratio (by weight) of the hydrophilic sequence (s) on the hydrophobic sequence (s) of the polymer is preferably between 10/1 and 1000/1.
- the cationic polymer or polymers comprising at least one hydrophobic block and at least one hydrophilic block may represent from 0.1% to 20% by weight, preferably from 0.5% to 10% by weight, and more particularly from 1 to 5% by weight relative to the total weight of the final composition.
- the nanoemulsions according to the present invention preferably comprise at least one nonionic amphiphilic lipid and / or at least one anionic amphiphilic lipid.
- the silicone surfactants that can be used according to the invention are silicone compounds comprising at least one oxyethylenated chain -OCH 2 CH 2 - and / or oxypropylene -OCH 2 CH 2 CH 2 -. Silicone surfactants that may be used according to the present invention include those described in US-A-5364633 and US-A-5411744.
- the alkyl radical is a methyl radical
- x is an integer ranging from 2 to 6
- y is an integer ranging from 4 to 30.
- silicone surfactants of formula (1) of the compounds of formula (III): H - (OCH 2 CH 2 ) y - (CH 2 ) 3 - [(CH 3 ) 2 SiO] A ' - (CH 2 ) 3 - (OCH 2 CH 2 ) y - OH (III) wherein A 'and y are integers ranging from 10 to 20.
- DC 5329, DC 7439-146, DC 2-5695 and Q4-3667 may be used.
- Compounds DC 5329, DC 7439-146, DC 2-5695 are compounds of formula (II) wherein A is respectively 22, B is 2 and y is 12; A is 103, B is 10 and y is 12; A is 27, B is 3 and y is 12.
- Compound Q4-3667 is a compound of formula (III) where A is and y is 13.
- the mixed esters of fatty acid or of fatty alcohol, of carboxylic acid and of glycerol, usable as surfactants in the nanoemulsion according to the invention may be chosen in particular from the group comprising mixed esters of fatty acid or of fatty alcohol having an alkyl chain having 8 to 22 carbon atoms, and alpha-hydroxy acid and / or succinic acid, with glycerin.
- the alpha-hydroxy acid may be, for example, citric acid, lactic acid, glycolic acid, malic acid and mixtures thereof.
- the alkyl chain of fatty acids or alcohols from which the mixed esters used in the nanoemulsion of the invention may be derived may be linear or branched, saturated or unsaturated. It may include stearate, isostearate, linoleate, oleate, behenate, arachidonate, palmitate, myristate, laurate, caprate, isostearyl, stearyl, linoleyl, oleyl, behenyl, myristyl, lauryl, capryl and mixtures thereof.
- mixed esters which may be used in the nanoemulsion of the invention, mention may be made of the mixed ester of glycerin and of the mixture of citric, lactic, linoleic and oleic acids (CTFA name: Glyceryl citrate / lactate / linoteate / oleate) marketed by Hüls under the name Imwitor 375; the mixed ester of succinic acid and isostearyl alcohol with glycerin (CTFA name: Isostearyl diglyceryl succinate) marketed by the company Huls under the name Imwitor 780 K; the mixed ester of citric acid and stearic acid with glycerol (CTFA name: Glyceryl stearate citrate) sold by Hüls under the name Imwitor 370; the mixed ester of lactic acid and stearic acid with glycerin (CTFA name: Glyceryl stearate lactate) sold by Danisco under the
- the fatty acid and sugar esters that can be used as surfactants in the nanoemulsion according to the invention are preferably solid at a temperature of less than or equal to 45 ° C. and may be chosen especially from the group comprising esters or mixtures of C 8 -C 22 fatty acid esters and sucrose, maltose, glucose or fructose, and esters or mixtures of C 14 -C 22 fatty acid esters and methylglucose.
- the C 8 -C 22 or C 14 -C 22 fatty acids forming the fatty unit of the esters that can be used in the nanoemulsion of the invention comprise a linear saturated or unsaturated alkyl chain, comprising respectively from 8 to 22 or from 14 to 22 carbon atoms.
- the fatty unit of the esters may in particular be chosen from stearates, behenates, arachidonates, palmitates, myristates, laurates, caprates and their mixtures. Stearates are preferably used.
- monoesters of glucose or maltose such as o-hexadecanoyl-6-D-glucoside methyl and o-
- the fatty alcohol and sugar ethers which can be used as surfactants in the nanoemulsion according to the invention are solid at a temperature of less than or equal to 45 ° C. and can be chosen in particular from the group comprising ethers or ether mixtures.
- the C 8 -C 22 or C 14 -C 22 fatty alcohols forming the fatty unit of the ethers that can be used in the nanoemulsion of the invention comprise a linear saturated or unsaturated alkyl chain, comprising respectively 8 to 22 or 14 to 22 carbon atoms.
- the fatty unit of the ethers may be chosen in particular from decyl, cetyl, behenyl, arachidyl, stearyl, palmityl, myristyl, lauryl, capryl, hexadecanoyl, and mixtures thereof such as cetearyl.
- alkylpolyglucosides such as decyl glucoside and lauryl glucoside marketed for example by Henkel under the respective names Plantaren 2000 and Plantaren 1200, cetostearyl glucoside. optionally mixed with cetostearyl alcohol, sold for example under the name Montanov 68 by the company Seppic, under the name Tego-care CG90 by the company Goldschmidt and under the name Emulgade KE3302 by Henkel, and arachidyl glucoside for example in the form of the mixture of arachidic and behenic alcohols and arachidyl glucoside sold under the name Montanov 202 by the company Seppic.
- cetostearyl alcohol sold for example under the name Montanov 68 by the company Seppic
- Tego-care CG90 by the company Goldschmidt
- Emulgade KE3302 by Henkel
- arachidyl glucoside for example in the form of the mixture of arachidic
- Sucrose monostearate, sucrose distearate, sucrose tristearate and mixtures thereof, methyl glucose and polyglycerol-3 distearate and alkyl polyglucosides are more particularly used as surfactants.
- the fatty esters of glycerol, usable as surfactants in the nanoemulsion according to the invention, solid at a temperature of less than or equal to 45 ° C. may be chosen especially from the group comprising esters formed of at least one acid containing an alkyl chain linear saturated, having from 16 to 22 carbon atoms, and from 1 to 10 glycerol units.
- esters formed of at least one acid containing an alkyl chain linear saturated, having from 16 to 22 carbon atoms, and from 1 to 10 glycerol units One or more of these glycerol fatty esters may be used in the nanoemulsion of the invention.
- esters may especially be chosen from stearates, behenates, arachidates and palmitates, and mixtures thereof. Stearates and palmitates are preferably used.
- CTFA names Polyglyceryl-10 stearate, Polyglyceryl-10 distearate, Polyglyceryl-10 tristearate, Polyglyceryl-10 pentastearate
- CTFA name Polyglyceryl-2 stearate
- the fatty esters of sorbitan that can be used as surfactants in the nanoemulsion according to the invention are solid at a temperature of less than or equal to 45 ° C. and are chosen from the group comprising the C 16 -C 22 fatty acid esters and sorbitan esters. and C 16 -C 22 fatty acid esters and oxyethylenated sorbitan. They are formed of at least one fatty acid comprising at least one saturated linear alkyl chain, having respectively from 16 to 22 carbon atoms, and sorbitol or ethoxylated sorbitol.
- the oxyethylenated esters generally comprise from 1 to 100 units of ethylene glycol and preferably from 2 to 40 units of ethylene oxide (EO).
- esters may especially be chosen from stearates, behenates, arachidates, palmitates, and mixtures thereof. Stearates and palmitates are preferably used.
- sorbitan monostearate (CTFA name: Sorbitan stearate) sold by ICI under the name Span 60
- sorbitan monopalmitate (CTFA name: Sorbitan). palmitate) sold by ICI under the name Span 40
- sorbitan tristearate 20 OE (CTFA name: Polysorbate 65) sold by ICI under the name Tween 65.
- the ethoxylated fatty ethers which are solid at a temperature of less than or equal to 45 ° C. which can be used as surfactants in the nanoemulsion according to the invention, are preferably ethers formed from 1 to 100 ethylene oxide units and from at least one chain. of fatty alcohol having from 16 to 22 carbon atoms.
- the fatty chain of the ethers may in particular be chosen from behenyl, arachidyl, stearyl and cetyl units, and mixtures thereof such as cetearyl.
- ethoxylated fatty ethers By way of example of ethoxylated fatty ethers, mention may be made of behenic alcohol ethers comprising 5, 10, 20 and 30 units of ethylene oxide (CTFA names: Beheneth-5, Beheneth-10, Beheneth-20, Beheneth-30), such as the products sold under the names Nikkol BB5, BB10, BB20, BB30 by the company Nikko , and the stearyl alcohol ether comprising 2 ethylene oxide units (CTFA name: Steareth-2), such as the product sold under the name Brij 72 by the company ICI.
- CTFA names: Beheneth-5, Beheneth-10, Beheneth-20, Beheneth-30 such as the products sold under the names Nikkol BB5, BB10, BB20, BB30 by the company Nikko
- CTFA name: Steareth-2 the stearyl alcohol ether comprising 2 ethylene oxide units
- the solid ethoxylated fatty esters at a temperature of less than or equal to 45 ° C. which can be used as surfactants in the nanoemulsion according to the invention, are esters formed from 1 to 100 ethylene oxide units and at least one ethylene oxide chain. fatty acid having from 16 to 22 carbon atoms.
- the fatty chain of the esters may especially be chosen from stearate, behenate, arachidate and palmitate units, and mixtures thereof.
- ethoxylated fatty esters By way of example of ethoxylated fatty esters, mention may be made of the stearic acid ester comprising 40 ethylene oxide units, such as the product sold under the name Myrj 52 (CTFA name: PEG-40 stearate) by the company ICI as well as the behenic acid ester comprising 8 units of ethylene oxide (CTFA name: PEG-8 behenate), such as the product sold under the name Compritol HD5 ATO by the company Gattefosse.
- CTFA name: PEG-40 stearate the product sold under the name Myrj 52
- behenic acid ester comprising 8 units of ethylene oxide CFA name: PEG-8 behenate
- the block copolymers of ethylene oxide (A) and of propylene oxide (B) that can be used as surfactants in the nanoemulsion according to the invention may be chosen in particular from block copolymers of formula (I): HO (C 2 H 4 O) x (C 3 H 6 O) y (C 2 H 4 O) zH (I) in which x, y and z are integers such that x + z is from 2 to 100 and y is from 14 to 60, and mixtures thereof, and more particularly from block copolymers of formula (I) having an HLB ranging from 2 to 16.
- the alkyl ether citrates which can be used as surfactants in the nanoemulsion according to the invention may be chosen in particular from the group comprising monoesters, diesters or triesters formed by citric acid and at least one oxyethylenated fatty alcohol, comprising a linear or branched alkyl chain. , saturated or unsaturated, having from 8 to 22 carbon atoms, and having from 3 to 9 ethoxylated groups, and mixtures thereof. It is indeed possible to use a mixture of one or more of these citrates in the nanoemulsion of the invention.
- citrates can be chosen, for example, from mono-, di- and tri-esters of citric acid and ethoxylated lauric alcohol, comprising from 3 to 9 ethoxylated groups, sold by Witco under the name Witconol EC, in particular Witconol EC 2129 which is predominantly a dilaureth-9 citrate, and Witconol EC 3129 which is predominantly a trilaureth-9 citrate.
- the alkyl ether citrates used as surfactants are preferably employed in neutralized form at a pH of about 7, the neutralizing agent being chosen from inorganic bases such as sodium hydroxide, potassium hydroxide, ammonia, and bases.
- organic compounds such as mono-, di- and tri-ethanolamine, aminomethylpropanediol-1,3, N-methylglucamine, basic amino acids such as arginine and lysine, and mixtures thereof.
- n and n ' are mean values and therefore are not necessarily integers.
- n it is advantageous to choose a value ranging from 5 to 60 and even more preferentially from 10 to 30.
- the radical R and / or R ' is chosen from linear alkenyl radicals comprising from 8 to 22 and preferably from 14 to 22 carbon atoms. It may be for example hexadecenyl radical having 16 carbon atoms or octadecenyl radical having 18 carbon atoms.
- the acid -COOH function of the surfactants of formulas (I) and (II) is generally found in the nanoemulsion of the invention, in neutralized form with a neutralization agent, the neutralization agent being chosen for example from inorganic bases.
- a neutralization agent such as sodium hydroxide, potassium hydroxide, ammonia, and organic bases such as mono-, di- and tri-ethanolamine, aminomethylpropanediol-1,3, N-methyl-glucamine, basic amino acids such as arginine and lysine, and mixtures thereof.
- the surfactant can be introduced into the aqueous phase or into the oily phase of the nanoemulsion.
- the amount of amphiphilic lipid ranges from 0.2 to 15% by weight and preferably from 1 to 8% by weight relative to the total weight of the nanoemulsion.
- the ratio by weight of the amount of the oily phase to the amount of amphiphilic lipid ranges from 1 to 10 and preferably from 1.2 to 6.
- the term “amount of oily phase” refers to the total amount of the constituents of the this phase without including the amount of amphiphilic lipid.
- the nanoemulsion of the invention may further contain one or more additional ionic amphiphilic lipids different from those described above.
- Their addition, as an additive, has the particular objective of further improving the stability of the dispersion.
- the cationic amphiphilic lipids used in the nanoemulsions of the invention are preferably chosen from the group consisting of quaternary ammonium salts, fatty amines and their salts.
- the alkyl radicals R 15 may be linear or branched and more particularly linear.
- R 15 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl radical and more particularly a methyl or ethyl radical.
- the sum x + y + z is from 1 to 10.
- R 16 is a hydrocarbon radical R 20, it may be long and contain from 12 to 22 carbon atoms or short and have from 1 to 3 carbon atoms.
- R 18 is a hydrocarbon radical R 22 , it preferably has 1 to 3 carbon atoms.
- R 17 , R 19 and R 21 which are identical or different, are chosen from linear or branched, saturated or unsaturated C 11 -C 21 hydrocarbon radicals, and more particularly from C 11 -C 15 alkyl and alkenyl radicals. 21 , linear or branched, saturated or unsaturated.
- x and z identical or different, are 0 or 1.
- y is 1.
- the anion is preferably a halide (chloride, bromide or iodide) or an alkyl sulphate more particularly methyl sulphate.
- a halide chloride, bromide or iodide
- an alkyl sulphate more particularly methyl sulphate.
- methanesulphonate, phosphate, nitrate, tosylate an anion derived from an organic acid such as acetate or lactate or any other anion compatible with ammonium with an ester function.
- the anion X - is even more particularly chloride or methylsulfate.
- R 17 , R 19 and R 21 which are identical or different, are chosen from linear or branched, saturated or unsaturated C 13 -C 17 hydrocarbon radicals and preferably from linear C 13 -C 17 alkyl and alkenyl radicals or branched, saturated or unsaturated.
- the hydrocarbon radicals are linear.
- the compounds of formula (VII) such as the salts (especially chloride or methylsulfate) of diacyloxyethyl dimethyl ammonium, diacyloxyethyl hydroxyethyl methyl ammonium, monoacyloxyethyl dihydroxyethyl methyl ammonium, triacyloxyethyl methyl ammonium, monoacyloxyethyl hydroxyethyl dimethyl ammonium and their mixtures.
- the acyl radicals preferably have from 14 to 18 carbon atoms and come more particularly from a vegetable oil such as palm oil or sunflower oil. When the compound contains more than one acyl radical, the latter may be identical or different.
- These products are obtained for example by direct esterification of triethanolamine, triisopropanolamine, alkyldiethanolamine or alkyldiisopropanolamine optionally oxyalkylenated on fatty acids or mixtures of fatty acids of plant or animal origin or by transesterification of their esters methyl.
- This esterification is followed by a quaternization using an alkylating agent such as an alkyl halide (preferably methyl or ethyl), a dialkyl sulphate (methyl or preferably ethyl), methyl methanesulphonate, methyl paratoluenesulfonate, glycol or glycerol chlorohydrin.
- an alkylating agent such as an alkyl halide (preferably methyl or ethyl), a dialkyl sulphate (methyl or preferably ethyl), methyl methanesulphonate, methyl paratoluenesulfonate,
- Such compounds are, for example, sold under the names DEHYQUART by the company HENKEL, STEPANQUAT by the company STEPAN, NOXAMIUM by the company CECA, REWOQUAT WE 18 by the company REWO-WITCO.
- composition according to the invention preferably contains a mixture of quaternary ammonium mono, di and triester salts with a majority by weight of diester salts.
- a mixture of ammonium salts it is possible to use, for example, the mixture containing 15 to 30% by weight of acyloxyethyl dihydroxyethyl methyl ammonium methyl sulphate, 45 to 60% of diacyloxyethyl hydroxyethyl methyl ammonium methyl sulphate and 15 to 30% of methyl sulphate.
- triacyloxyethyl methyl ammonium the acyl radicals having from 14 to 18 carbon atoms and coming from partially hydrogenated palm oil.
- ammonium salts containing at least one ester function described in US-A-4874554 and US-A-4137180.
- tetraalkylammonium chlorides for example dialkyldimethylammonium or alkyltrimethylammonium chlorides, in which the alkyl radical contains approximately from 12 to 22 carbon atoms, are preferred.
- dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl radical contains approximately from 12 to 22 carbon atoms.
- behenyltrimethylammonium chloride is the most preferred quaternary ammonium salt.
- the nanoemulsion contains one or more additional cationic or anionic amphiphilic lipids, they are present in the nanoemulsions of the invention, preferably in concentrations ranging from 0.01 to 10% by weight. relative to the total weight of the nanoemulsion and more particularly from 0.2 to 5% by weight.
- Isobutylene oligomers with a molecular weight of less than 1000 and their mixtures with polyisobutylenes with a molecular weight greater than 1000 and preferably between 1000 and 15000 are preferably used.
- the esters of liquid carboxylic acids can be mono, di, tri or tetracarboxylic.
- the total carbon number of the esters is generally greater than or equal to 10 and preferably less than 100 and more particularly less than 80.
- the monocarboxylic acid esters are in particular saturated or unsaturated, linear or branched C 1 -C 26 aliphatic acid monoesters and saturated or unsaturated aliphatic alcohols, linear or branched C 1 -C 26 , the total number of carbon of the esters being generally greater than or equal to 10.
- esters mentioned above it is preferred to use ethyl palmitate, isopropyl palmitate, ethyl-2-hexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as myristate of isopropyl, butyl, cetyl, 2-octyldodecyl, hexyl stearate, butyl stearate, isobutyl stearate; dioctyl malate, hexyl laurate, 2-hexyldecyl laurate and isononyl isononanate, cetyl octanoate.
- alkyl myristates such as myristate of isopropyl, butyl, cetyl, 2-octyldodecyl, hexyl stearate, butyl stearate, isobutyl stearate; dioctyl malate,
- the nanoemulsions according to the invention comprise an amount of oil preferably ranging from 2 to 40% by weight relative to the total weight of the emulsion and more particularly from 4 to 30% by weight and preferably from 8 to 20% by weight. in weight.
- compositions according to the invention further comprise at least one aminosilicone.
- hydrocarbon radicals are alkyl radicals, especially C 1 -C 10 and in particular methyl radicals, fluoroalkyl radicals, aryl radicals and in particular phenyl radicals, and alkenyl radicals and in particular vinyl radicals; other types of radicals which may be bonded either directly or via a hydrocarbon radical to the siloxane chain include hydrogen, halogens and in particular chlorine, bromine or fluorine, thiols, alkoxy radicals, polyoxyalkylene (or polyether) radicals and in particular polyoxyethylene and / or polyoxypropylene radicals, hydroxyl or hydroxyalkyl radicals, amide groups, acyloxy or acyloxyalkyl radicals, amphoteric or betaine groups, anionic groups such as carboxylates , thioglycolates, sulfosuccinates, thiosulphates, phosphates and sulphates, this list being of course in no way limiting ("organomodified
- Silicones falling within this class are the silicones marketed by GOLDSCHMIDT under the names ABIL QUAT 3270, ABIL QUAT 3272 and ABIL QUAT 3474.
- the amino silicones can be in the form of an oil, aqueous solutions, alcoholic or aqueous-alcoholic, in the form of dispersion or emulsion.
- a particularly interesting embodiment is their use in the form of emulsions, in particular in the form of microemulsions or nanoemulsions.
- Cationic Emulsion DC 929 can be used by the Dow Corning Company which comprises, in addition to amodimethicone, a cationic surfactant derived from tallow fatty acid called Tallowtrimonium (CTFA), in association with a nonionic surfactant known as "Nonoxynol 10".
- CFA cationic surfactant derived from tallow fatty acid
- Another commercial product that can be used according to the invention is the product sold under the name Dow Corning Q2 7224 by the Dow Company.
- the aminosilicone is present at a concentration of between 0.05 and 10% by weight relative to the total weight of the emulsion, preferably between 0.1 and 5% by weight and more particularly from 0.3 to 3% by weight. % in weight.
- the emulsions according to the present invention may contain solvents, in particular to improve, if necessary, the transparency of the formulation.
- Solvents such as those mentioned above are present in the emulsions of the invention in concentrations ranging, preferably, from 0.01 to 30% by weight relative to the total weight of the emulsion.
- the emulsions of the invention may contain water-soluble or fat-soluble active agents having a cosmetic or dermopharmaceutical activity.
- the liposoluble active agents are in the oily globules of the emulsion, while the water-soluble active agents are in the aqueous phase of the emulsion.
- active ingredients examples include vitamins and their derivatives such as vitamin E, vitamin E acetate, vitamin C and its esters, vitamin B, vitamin A alcohol or retinol, vitamin A acid or retinoic acid and its derivatives, provitamins such as panthenol, vitamin A palmitate, niacinamide, ergocalciferol, antioxidants, essential oils, humectants, silicone sunscreens or not preservatives, sequestering agents, softeners, colorants, viscosity modifying agents, foam modifiers, foam stabilizers, pearlescent agents, pigments, moisturizing agents, anti-dandruff agents, antiseborrhoeic agents, proteins, ceramides, pseudoceramides, C 16 -C 40 linear or branched chain fatty acids such as 18-methyl eicosanoic acid, plasticizers, hydroxy acids, electrolytes, polymers, in particular cationic polymers and perfumes .
- vitamins and their derivatives such as vitamin E, vitamin E a
- the oil globules of the emulsions of the invention preferably have an average size ranging from 20 to 150 nm, more preferably from 30 to 100 nm and even more particularly from 40 to 80 nm.
- the nanoemulsions according to the invention generally have a transparent to bluish appearance. Their transparency is measured by a transmittance coefficient at 600 nm ranging from 10 to 90% or by a turbidity ranging from 60 to 600 NTU and preferably from 70 to 400 NTU, turbidity measured with the portable turbidimeter HACH - Model 2100 P.
- the nanoemulsions of the invention may be obtained by a process, characterized in that the aqueous phase and the oily phase are mixed, with vigorous stirring, at an ambient temperature of less than 45 ° C. and then a high homogenization is carried out. pressure at a pressure greater than 5.10 7 Pa and preferably ranging from 6.10 7 to 18.10 7 Pa.
- Such a process makes it possible to carry out, at ambient temperature, nanoemulsions that are compatible with heat-sensitive active compounds, and that can contain significant amounts of oils. and especially perfumes that contain fat, without denaturing.
- compositions for topical use such as a cosmetic or dermopharmaceutical composition, characterized in that that it consists of a nanoemulsion as defined above or that it comprises such a nanoemulsion.
- compositions according to the invention can be used for washing, cleaning and removing makeup keratin materials such as hair, skin, eyelashes, eyebrows, nails, mucous membranes.
- compositions of the invention may more particularly be in the form of shampoos, conditioners to be rinsed or not, compositions for permanent, straightening, coloring or bleaching, or in the form of compositions to be applied before or after staining. , discoloration, permanent or straightening or between the two stages of a perm or straightening.
- compositions may also be styling lotions, blow-drying lotions, fixing (lacquer) and styling compositions such as, for example, gels or foams.
- the lotions may be packaged in various forms, in particular in vaporizers, pump bottles or in aerosol containers to ensure application of the composition in vaporized form or in the form of foam. Such forms of packaging are indicated, for example, when it is desired to obtain a spray, a lacquer or a mousse for fixing or treating the hair.
- composition according to the invention when packaged in the form of an aerosol in order to obtain a lacquer or an aerosol foam, it comprises at least one propellant which may be chosen from volatile hydrocarbons such as n-butane, propane, propionic acid and propellant. isobutane, pentane, chlorinated and / or fluorinated hydrocarbons and mixtures thereof. It is also possible to use carbon dioxide, nitrous oxide, dimethyl ether, nitrogen or compressed air as propellant.
- propellant may be chosen from volatile hydrocarbons such as n-butane, propane, propionic acid and propellant. isobutane, pentane, chlorinated and / or fluorinated hydrocarbons and mixtures thereof. It is also possible to use carbon dioxide, nitrous oxide, dimethyl ether, nitrogen or compressed air as propellant.
- compositions in accordance with the invention may be used for the care and / or the makeup of keratin materials such as the hair, the skin of the body and / or the face, the eyelashes, the eyebrows, the nails and the mucous membranes.
- Another subject of the invention is the use of the emulsions as defined above as a base for care products and / or make-up and / or make-up removal for the skin of the body and / or of the face and / or the scalp and / or the hair and / or the nails and / or the eyelashes and / or the eyebrows and / or the mucous membranes (for example the lips), such as lotions, serums, milks, creams, eaux de toilette .
- the invention also relates to a non-therapeutic method for the care of the skin, the hair, the eyelashes, the eyebrows, the nails, the mucous membranes or the scalp, characterized in that it is applied to the skin, hair, eyelashes, eyebrows, nails, mucous membranes or scalp a nanoemulsion as defined above.
- An emulsion is obtained in which the size of the oil globules is approximately 63 nm. This composition is stable storage for 2 months at room temperature and at 45 ° C.
- the composition has a turbidity of 375 NTU and a viscosity of 650 mPa.s (cP).
- the viscosity is measured with a Rheomat 108 rheometer with a velocity gradient of 200s -1 at 25 ° C. (mobile 3).
- Hair treated with this composition is easy to disentangle, soft and shiny.
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FR0000792A FR2804014B1 (fr) | 2000-01-21 | 2000-01-21 | Nanoemulsion a base de lipides amphiphiles et de polymeres cationiques et utilisations |
FR0000792 | 2000-01-21 |
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EP1129684A2 EP1129684A2 (fr) | 2001-09-05 |
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EP1129684B1 true EP1129684B1 (fr) | 2006-06-21 |
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EP (1) | EP1129684B1 (ja) |
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CA (1) | CA2332466A1 (ja) |
DE (1) | DE60028921T2 (ja) |
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US9744116B2 (en) | 2013-09-18 | 2017-08-29 | L'oreal | High color intensity and easily removable mascara |
CN107249560A (zh) * | 2015-02-27 | 2017-10-13 | 那野伽利阿株式会社 | 高分子处理剂 |
WO2016137006A1 (ja) * | 2015-02-27 | 2016-09-01 | ナノキャリア株式会社 | ポリマーミセル担体組成物およびポリマーミセル組成物 |
FR3076213B1 (fr) * | 2017-12-29 | 2020-01-17 | L'oreal | Composition sous forme de nanoemulsion huile-dans-eau comprenant au moins un tensioactif cationique, au moins un polyol, une faible teneur en eau, et au moins un corps gras |
FR3076219B1 (fr) * | 2017-12-29 | 2020-01-17 | L'oreal | Composition cosmetique sous forme de nanoemulsion huile-dans-eau comprenant au moins 40 % de corps gras, au moins un tensioactif cationique et de l'eau |
FR3076215B1 (fr) * | 2017-12-29 | 2020-10-02 | Oreal | Composition cosmetique foisonnee sous forme d'une nanoemulsion comprenant au moins 20% de corps gras, au moins un tensioactif cationique, un gaz et de l'eau |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4733677A (en) * | 1986-11-04 | 1988-03-29 | Dow Corning Corporation | Hair fixative composition containing cationic organic polymer and polydiorganosiloxane microemulsions |
FR2760970B1 (fr) * | 1997-03-18 | 2000-03-10 | Oreal | Nanoemulsions a base de lipides amphiphiles non-ioniques et de silicones aminees et utilisations |
GB9808310D0 (en) * | 1998-04-20 | 1998-06-17 | Unilever Plc | Shampoo compositions |
US6533873B1 (en) * | 1999-09-10 | 2003-03-18 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Suspending clear cleansing formulation |
-
2000
- 2000-01-21 FR FR0000792A patent/FR2804014B1/fr not_active Expired - Fee Related
- 2000-12-14 EP EP00403527A patent/EP1129684B1/fr not_active Expired - Lifetime
- 2000-12-14 DE DE60028921T patent/DE60028921T2/de not_active Expired - Lifetime
- 2000-12-14 AT AT00403527T patent/ATE330579T1/de not_active IP Right Cessation
- 2000-12-14 ES ES00403527T patent/ES2265897T3/es not_active Expired - Lifetime
-
2001
- 2001-01-17 BR BR0100335-6A patent/BR0100335A/pt not_active Application Discontinuation
- 2001-01-18 CA CA002332466A patent/CA2332466A1/fr not_active Abandoned
- 2001-01-22 US US09/765,675 patent/US20010028887A1/en not_active Abandoned
- 2001-01-22 JP JP2001013866A patent/JP2001214081A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
FR2804014A1 (fr) | 2001-07-27 |
BR0100335A (pt) | 2001-10-09 |
FR2804014B1 (fr) | 2002-10-18 |
US20010028887A1 (en) | 2001-10-11 |
DE60028921D1 (de) | 2006-08-03 |
ES2265897T3 (es) | 2007-03-01 |
EP1129684A2 (fr) | 2001-09-05 |
EP1129684A3 (fr) | 2001-11-14 |
DE60028921T2 (de) | 2007-01-11 |
JP2001214081A (ja) | 2001-08-07 |
CA2332466A1 (fr) | 2001-07-21 |
ATE330579T1 (de) | 2006-07-15 |
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